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Southwest Is Playing Games With Calendar Opening Days, Check Your Bookings

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Southwest Calendar Extension Day Games

Southwest Calendar Extension Day Games

I wanted to put together a quick PSA post about the Southwest calendar extension day games. It is no secret that Southwest is not a favorite of mine. I used to put up with a lot of their shortcomings because their award program was so flexible and they were often cheaper. They lost that leg to stand on though, during the pandemic now that almost all airlines allow free cancellations. Their flight prices have started to shoot up too, outside of hub routes, and they are often more expensive than even the big 3 (Delta, United, American) in my searches. Not to mention all of the connections from our non hub airport.

Southwest’s Need For Calendar Release Days

One of my biggest gripes with the program is that they only release a partial calendar and bump it out every so often. Other airlines are able to schedule near a year out but the low cost carriers only do 6 and 7 month chunks. I could deal with that when Southwest was a low cost carrier, but they are far from that place these days.

Having said that, Southwest schedule release day has always been a pretty big day. So much so that people figured out tips and tricks to get to the calendar 15 minutes before everyone else and had quick searches already set up etc. That is because there were always deals to be had. That isn’t the case anymore.

Southwest Calendar Extension Day Games

Southwest Is Price Gouging Customers On Schedule Open Day

Southwest has gone direct opposite of that and, as my buddy Derrick at ToP says, have laid the ultimate honey trap. They price flights out at premiums on release day. It is so obvious what they are doing because they will even lower the prices later in the day once demand drops. They are trying to grab the excitement of calendar release day and hit you up for more money, or points. You can always adjust the booking later of course, but they are hoping people forget. Plus, if you booked with cash you now have a voucher instead of money back. That is why you should always make speculative bookings, or early bookings, with points. It is much easier to deal with price drops that way.

Case in point, my friend Dave booked flights to Hawaii for June right when the calendar opened. He paid out the nose at 57,000 points per person. He has 2 companion passes which made the price easier to swallow when comparing that to the competition. He checked his flights today and rebooked them at 36,000 miles each. That is an astonishing price drop of 21,000 miles per person…IN ONE DAY.

Southwest Calendar Extension Day Games: Final Thoughts

These games being played by Southwest are contrary to the customer friendly atmosphere that the airline was built on. They continue to backslide towards the big 3 all while playing their long time customer’s heart strings drumming up friendly memories of old. Don’t fall for their games, check your bookings yesterday and let me know if they dropped today down in the comments.

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Mark Ostermann
Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

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  1. I too have noticed what you mentioned about release day price inflation, however you miss one caveat of this. The “prime” time slots do not always go down after release day due to them being lower in inventory. This makes getting them on release day a benefit. For people like my 70 year old mother who thinks a 600am flight is way too early and arriving past 1000pm is way too late, getting the mid-day flight on release day is the best time to buy. WN seems to lower pricing on the less desirable times after release day like Saturday morning from a desirable vacation destination.

  2. Great post! I was SHOCKED when I went in to check flights yesterday morning. I just checked now after your post, and you are right, the same flights I looked at yesterday are way lower!! WOW!!! I’m not a fan of this. I will keep in mind and not worry about the calendar opening date. I also agree with your above comment of the value overall with the connections, and time. Thank you.

  3. Like every airline Southwest has its positives and negatives.
    You have to constantly garden your reservations as hotel programs and airlines prey on stupidity with their overcharging more frequently especially as more and more programs move towards dynamic or seasonal pricing typically.Like the stock market its cyclical.
    Let the uneducated buyer beware.And its ok to have a bias against any airline or hotel program as long as you can separate the good from the bad at the end of the day.Takes a lot of work on the buyers side.I just canceled a 200k business award on United recently and booked it in business again for 55k on a better aircraft/carrier by constantly checking availability.Its gotten much harder but not impossible either.

  4. SW is not the only to do this. United has also done this. I have gone back and rebooked my United flight because the price in points dropped. I have learned to regularly keep an eye on flights whether I pay cash or points. SW is not a fit for everyone. Once you fly with them for a while you actually get it and it works. I actually like their no assign seating, I prefer that to the price gauging that many other airlines do. Charging to get a seat is wrong! that can substantially increase your flight price which is wrong. I am looking forward to this getting regulated. I too like many others appreciate the CP without it our family travel would also be half of what we do. Their booking process is simple. No bells and whistles, simple site that gets to the point. I still get better customer service from SW flight attendants versus United and American Airlines. I dread United their flight attendants seem to totally hate their job. I fly then when it is out of necessity. When at all possible I avoid them.

  5. Regarding fare competitiveness, it’s going to have to be a pretty huge difference in price for the CP not to work out in our favor. I’d be willing to bet you a beer that you couldn’t find ONE example where the fare for 2 people going from point A to B was cheaper than someone using a CP.
    That being said, if I’m flying alone, or when I lose my CP, I’m definitely shopping around for the best fare.
    Good post today!

    • Oh no doubt, I wasn’t saying that it isn’t almost always going to be cheaper 2 to 1 but was saying it isn’t really half off. A lot of people like to just add up their flight costs for the year and say the Companion Pass saved me that amount which isn’t really the case was my point. Just saying people overvalue it a bit imo but it is still really valuable no doubt.

  6. As you said “It is no secret that Southwest is not a favorite of mine. ” Do you think that might create some bias when writing about them?
    That being said, whatever SWA shortcomings, I’ll gladly overlook them because of the Companion Pass. With out that, my travel would literally be half of what it is as my wife and i travel quite a bit to see kids and grandkids. She really doesn’t like SWA when it comes to no seat selection but realizes it’s eaither that or don’t go places because of the cost.
    And regarding higher pricing, how many routes did you compare to see if these “games” were widespread or just on a few select routes. and as you said, at least you can get the lower fare with minimal hassle. And while we are on the subject of refunds vs. credits… at least they don’t expire anymore.
    Anyway… that’s my .02.

    • I think people play into the Companion Pass being “half off” too much too. It is half off the Southwest fare but is that always the cheapest fare overall that you are booking? My guess is most of the time it is not (unless at a Southwest hub). Are you sometimes taking flights with connections in order to use it? What is that time worth to you? Etc. Something to consider when talking about the value proposition.

      People that know a lot more about Southwest (ones I talk about getting in early etc.) have been telling me this has been going on for a while now. My buddy sharing his price drop this morning sparked me into action no doubt though. They are relying on their good natured history to take advantage of people and I am going to point that out no matter who the airline is. That didn’t play a role at all.

      As I said their program used to be leaps and bounds better than anyone else but that has changed. Whether the shortcomings are worth it because of the CP, the preferred routing out of your airport or their pricing etc. is a personal decision. But they don’t have that competitive advantage anymore which means it all comes down to where you are and where you are flying, when that wasn’t always the case before.

      I can totally see where the program etc. works great for people though and I am glad it works for you. I would still avoid booking on calendar launch date though unless you already have the points in your Rapid Rewards account. Check back a day or two later and see if they dropped before transferring in is how I would play it (as someone that doesn’t use RR points a ton).


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